Triethylamine → HCID 69620892, 화합물

HRID 1628296노트

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HRID 1628296 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([NH:15][C:16](=[O:33])[C@@H:17]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([CH3:14])[CH:9]=2)[CH:7]=1.C(N(CC)CC)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH3:14][C:10]1[CH:9]=[C:8]([C:6]2[CH:5]=[C:4]([NH:15][C:16](=[O:33])[C@@H:17]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:3]=[C:2]([NH:1][S:42]([CH3:41])(=[O:44])=[O:43])[CH:7]=2)[CH:13]=[CH:12][N:11]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 69620893HCID 69620893, 화합물

생성물 1

HCID 69620892HCID 69620892, 화합물수율 47.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a 0° C. solution of 51.1D (512 mg, 1.16 mmol) and triethylamine (478 μl, 3.44 mmol) in CH2Cl2 (10 mL) under N2 was added methanesulfonyl chloride (available from Aldrich) (84.3 μl, 1.08 mmol) drop wise over 10 min. After stirring at 0° C. for 30 min, the reaction mixture was treated with saturated aqueous NaHCO3 (1 mL), diluted with water (10 mL), and extracted with CH2Cl2 (3×10 mL). Organic layers were combined, dried over MgSO4, and concentrated under reduced pressure. Purification of the residue by flash chromatography on silica gel using 0-70% EtOAc/CH2Cl2 provided title product 51.1E as white solid (268 mg, 43%).

후처리

  1. extractionextracted with CH2Cl2 (3×10 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customPurification of the residue by flash chromatography on silica gel using 0-70% EtOAc/CH2Cl2

출처 및 근거

ORD 기록
ord-7304fb8d49a44900b78c100b2a3392af
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785468B2

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